diethyl {2-[N-(pivaloyloxymethyl)-N-(p-toluenesulfonyl)amino]ethoxymethyl}phosphonate | 1170676-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl {2-[N-(pivaloyloxymethyl)-N-(p-toluenesulfonyl)amino]ethoxymethyl}phosphonate
• 英文别名: [2-(Diethoxyphosphorylmethoxy)ethyl-(4-methylphenyl)sulfonylamino]methyl 2,2-dimethylpropanoate；[2-(diethoxyphosphorylmethoxy)ethyl-(4-methylphenyl)sulfonylamino]methyl 2,2-dimethylpropanoate
• CAS: 1170676-94-4
• 化学式: C₂₀H₃₄NO₈PS
• 分子量: 479.532
• InChiKey: WRQYTDRURUKFTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diethyl {2-[N-(pivaloyloxymethyl)-N-(p-toluenesulfonyl)amino]ethoxymethyl}phosphonate 、 胸腺嘧啶 在 N,O-双三甲硅基乙酰胺 、 四氯化锡 、 水 、 碳酸氢钠 作用下， 以 乙腈 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 50.0h， 以83%的产率得到diethyl {2-[N-(5-methyl-1H,3H-pyrimidine-2,4-dion-1-ylmethyl)-N-(p-toluenesulfonyl)amino]ethoxymethyl}phosphonate
  参考文献：
  名称：

  Synthesis and antiviral activity evaluation of acyclic 2′-azanucleosides bearing a phosphonomethoxy function in the side chain

  摘要：

  Acyclic 2'-azanucleosides with a phosphonomethoxy function in the side chain were obtained by coupling of diethyl {2-[N-(pivaloyloxymethyl)-N-(p-toluenesulfonyl)amino]ethoxymethyl} phosphonate with the pyrimidine nucleobases via the Vorbruggen-type protocol. The compounds were evaluated in vitro for activity against a broad variety of RNA and DNA viruses. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.054
• 作为产物：
  描述：

  特戊酸氯甲酯 、 diethyl [2-(p-toluenesulfonylamino)ethoxy]methylphosphonate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以96%的产率得到diethyl {2-[N-(pivaloyloxymethyl)-N-(p-toluenesulfonyl)amino]ethoxymethyl}phosphonate
  参考文献：
  名称：

  Synthesis and antiviral activity evaluation of acyclic 2′-azanucleosides bearing a phosphonomethoxy function in the side chain

  摘要：

  Acyclic 2'-azanucleosides with a phosphonomethoxy function in the side chain were obtained by coupling of diethyl {2-[N-(pivaloyloxymethyl)-N-(p-toluenesulfonyl)amino]ethoxymethyl} phosphonate with the pyrimidine nucleobases via the Vorbruggen-type protocol. The compounds were evaluated in vitro for activity against a broad variety of RNA and DNA viruses. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.054

文献信息

• Synthesis and antiviral activity evaluation of acyclic 2′-azanucleosides bearing a phosphonomethoxy function in the side chain
  作者：Mariola Koszytkowska-Stawińska、Erik De Clercq、Jan Balzarini

  DOI：10.1016/j.bmc.2009.04.054

  日期：2009.6

  Acyclic 2'-azanucleosides with a phosphonomethoxy function in the side chain were obtained by coupling of diethyl 2-[N-(pivaloyloxymethyl)-N-(p-toluenesulfonyl)amino]ethoxymethyl} phosphonate with the pyrimidine nucleobases via the Vorbruggen-type protocol. The compounds were evaluated in vitro for activity against a broad variety of RNA and DNA viruses. (C) 2009 Elsevier Ltd. All rights reserved.